Water → 1,1,1,2,2,3,3,4,4-Nonafluoro-8-iodooctane

HRID 1267472Notes

Reaction equation

HRID 1267472 reaction equation
[I-:1].[Na+].CS(O[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])(=O)=O.O>CC(C)=O>[I:1][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([F:24])([F:23])[C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 120157881-Methanesulfonyloxy-5,5,6,6,7,7,8,8,8-nonafluorooctane

Product 1

HCID 120157891,1,1,2,2,3,3,4,4-Nonafluoro-8-iodooctaneYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (10.32 g, 68.88 mmol) was added to a solution of 1-methanesulfonyloxy-5,5,6,6,7,7,8,8,8-nonafluorooctane (8.5 g, 22.96 mmol) in acetone (300 ml), followed by heating under reflux for 12 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted twice with ethyl acetate. The combined organic layers were washed with 1% aqueous sodium thiosulfate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off to give 1-iodo-5,5,6,6,7,7,8,8,8-nonafluorooctane (8.6 g, Yield 93%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 12 hours
  3. extractionwas then extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with 1% aqueous sodium thiosulfate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-ed8c2c373927482db1be75d1311ff254
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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